Promoting Catalysis and Expanding the Scope of Organometallic Nucleophiles Utilized in the Nickel-Mediated Decarbonylative Cross- Coupling of Substituted Phthalimides
Dr. Jeffrey Johnson
A new method for synthesizing ortho-substituted benzamides has been developed through the nickel-mediated decarbonylative cross-coupling of substituted phthalimides with various diorganozinc reagents. This reaction demonstrates broad substrate scope, including both electron-rich and electronpoor aryl phthalimide substituents and a variety of commercially available and in situ generated diorganozinc reagents. However, this reaction suffers from two key limitations. First, it requires a stoichiometric equivalent of nickel, which limits its application in synthesis. Second, diorganozinc reagents are either pyrophoric or must be synthesized in situ. Efforts to promote catalysis include altering the phthalimide substituent, ligand, solvent, and catalyst used. Recent work has also focused on expanding the scope of nucleophiles to include boronic acids, which are safer and more commercially available, while optimizing reaction conditions of this new system.
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